N−H Imine as a Powerful Directing Group for Cobalt-Catalyzed Olefin Hydroarylation

Wengang Xu, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

42 Citations (Scopus)

Abstract

N-alkyl and N-aryl imines have been frequently used as directing groups in rhodium- and cobalt-catalyzed hydroarylation reactions of olefins and alkynes. However, the scope of such hydroarylation reactions has been limited by the difficulty of preparation of sterically hindered imines by condensation, and also by the steric bulkiness of the imine group itself. Reported herein is that an N−H imine serves as an alternative and highly effective directing group for cobalt-catalyzed hydroarylation of olefins, and unlocks many of the limitations associated with the previously employed N-aryl imine directing group. The power of this minimal nitrogen directing group is manifested in a fourfold ortho alkylation of benzophenone imine, and it occurs rapidly at ambient temperature.

Original languageEnglish
Pages (from-to)12731-12735
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number41
DOIs
Publication statusPublished - 2016 Oct 4
Externally publishedYes

Keywords

  • C−H activation
  • alkenes
  • alkylation
  • arenes
  • cobalt

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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